CA2009503A1 - Ethers of 1-benzyl-3-hydroxymethyl-indazole with aliphatic 2-hydroxyacids - Google Patents
Ethers of 1-benzyl-3-hydroxymethyl-indazole with aliphatic 2-hydroxyacidsInfo
- Publication number
- CA2009503A1 CA2009503A1 CA2009503A CA2009503A CA2009503A1 CA 2009503 A1 CA2009503 A1 CA 2009503A1 CA 2009503 A CA2009503 A CA 2009503A CA 2009503 A CA2009503 A CA 2009503A CA 2009503 A1 CA2009503 A1 CA 2009503A1
- Authority
- CA
- Canada
- Prior art keywords
- benzyl
- formula
- compounds
- aliphatic
- hydroxyacids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- AKQDXNFPEFHRLS-UHFFFAOYSA-N (1-benzylindazol-3-yl)methanol Chemical compound C12=CC=CC=C2C(CO)=NN1CC1=CC=CC=C1 AKQDXNFPEFHRLS-UHFFFAOYSA-N 0.000 title 1
- 125000001931 aliphatic group Chemical group 0.000 title 1
- 150000002170 ethers Chemical class 0.000 title 1
- -1 1-benzyl-indazol-3-yl Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Compounds and methods of preparation of compounds with the formula A-CH2-O-CRR'-COOR"' (I) where A is a 1-benzyl-indazol-3-yl nucleus of the formula (see formula II) R and R' may be the same or different and are H or C1-C5 alkyl, R"' is H or the residue of an aliphatic saturated alcohol having from 1 to 4 carbon atoms; and, when R"' is H, the salts thereof with pharmaceutically acceptable bases. The addition of a methylene group (-CH2-) between the 1-benzyl-indazol-3yl nucleus and the side claim (-O-CH2-COOR"') endows the compounds of Formula (I) with analgesic activity.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8947620A IT1230441B (en) | 1989-02-07 | 1989-02-07 | ETHERS OF THE INDAZOLE SERIES |
| IT47620A/89 | 1989-02-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2009503A1 true CA2009503A1 (en) | 1990-08-07 |
| CA2009503C CA2009503C (en) | 2000-04-11 |
Family
ID=11261479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002009503A Expired - Lifetime CA2009503C (en) | 1989-02-07 | 1990-02-07 | Ethers of 1-benzyl-3-hydroxymethyl-indazole with aliphatic 2-hydroxyacids |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US4999367A (en) |
| EP (1) | EP0382276B1 (en) |
| JP (1) | JP2870925B2 (en) |
| KR (1) | KR0145525B1 (en) |
| CN (2) | CN1046505C (en) |
| AR (1) | AR247386A1 (en) |
| AT (1) | ATE127115T1 (en) |
| AU (1) | AU624895B2 (en) |
| BG (1) | BG50273A3 (en) |
| CA (1) | CA2009503C (en) |
| CZ (1) | CZ280121B6 (en) |
| DD (2) | DD295363A5 (en) |
| DE (2) | DE69021902T2 (en) |
| DK (1) | DK0382276T3 (en) |
| EG (1) | EG19170A (en) |
| ES (1) | ES2020171T3 (en) |
| FI (1) | FI102678B (en) |
| GE (1) | GEP19971030B (en) |
| GR (2) | GR910300073T1 (en) |
| HU (1) | HU204793B (en) |
| IL (1) | IL93132A (en) |
| IN (1) | IN170957B (en) |
| IT (1) | IT1230441B (en) |
| LT (1) | LT3604B (en) |
| LV (1) | LV10612B (en) |
| NZ (1) | NZ232258A (en) |
| PE (1) | PE25091A1 (en) |
| PH (1) | PH26552A (en) |
| PL (2) | PL163720B1 (en) |
| PT (1) | PT93067B (en) |
| RO (1) | RO106252B1 (en) |
| RU (3) | RU2066318C1 (en) |
| SK (1) | SK56390A3 (en) |
| UA (1) | UA26852C2 (en) |
| YU (1) | YU47943B (en) |
| ZA (1) | ZA90644B (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1253703B (en) * | 1991-04-22 | 1995-08-23 | Angelini Francesco Ist Ricerca | USE OF ALCANOIC ACID METHODS OF INDAZOLE TO PREPARE AN ACTIVE DRUG IN THE TREATMENT OF AUTOIMMUNITARY DISEASES |
| IT1293795B1 (en) * | 1997-07-28 | 1999-03-10 | Angelini Ricerche Spa | DRUG ACTIVE IN REDUCING THE PRODUCTION OF MCP-1 PROTEIN |
| US5943270A (en) * | 1997-11-26 | 1999-08-24 | Intel Corporation | Two-transistor DRAM cell for logic process technology |
| US7514463B2 (en) | 2004-08-20 | 2009-04-07 | University Of Kansas | Lonidamine analogues and their use in male contraception and cancer treatment |
| ITMI20062254A1 (en) | 2006-11-24 | 2008-05-25 | Acraf | USE OF A METHOXY-ALCANOIC ACID OF THE INZOL TO PREPARE A PHARMACEUTICAL COMPOSITION |
| HRP20160457T1 (en) | 2008-03-07 | 2016-05-20 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | 1-BENZYL-3-HYDROXYMETHYLINDASOL DERIVATIVES AND THEIR USE IN THE TREATMENT OF DISEASES BASED ON EXPRESSION OF MCP-1 AND CX3CR1 |
| CN101952256B (en) * | 2008-03-07 | 2016-03-16 | 方济各安吉利克化学联合股份有限公司 | 1-benzyl-3-hydroxymethyl indazole derivatives and the purposes in the disease for the treatment of based on MCP-1, CX3CR1 and p40 expression thereof |
| AU2009221087B2 (en) | 2008-03-07 | 2013-12-05 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of MCP-1, CX3CR1 and p40 |
| BR112012002130A2 (en) * | 2009-08-03 | 2015-09-15 | Aziende Chimique Riunite Angelini Francesco A C R A F S P A | process for the preparation of compound and intermediate compound |
| UA108742C2 (en) | 2009-09-23 | 2015-06-10 | PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF MCP-1 MEDIATED DISEASES | |
| US8999292B2 (en) | 2012-05-01 | 2015-04-07 | Translatum Medicus Inc. | Methods for treating and diagnosing blinding eye diseases |
| CN104334173B (en) | 2012-05-01 | 2017-05-03 | 特兰斯拉图姆医学公司 | Methods for treating and diagnosing blinding eye diseases |
| JP2015521183A (en) | 2012-05-18 | 2015-07-27 | サノフイ | Pyridine derivatives and their use in the treatment of conditions associated with pathological thrombus formation |
| ES2612205T3 (en) | 2012-05-18 | 2017-05-12 | Sanofi | Pyrazole derivatives and their use as antagonists of LPAR5 |
| CN108047136B (en) * | 2017-12-20 | 2021-07-09 | 长春普华制药股份有限公司 | Refining method of benzydac |
| CA3144861A1 (en) * | 2019-06-25 | 2020-12-30 | Translatum Medicus, Inc. | Processes of making 2-((1-benzyl-1h-indazol-3-yl)methoxy)-2-methylpropanoic acid and its derivatives |
| CN113929627A (en) * | 2021-10-19 | 2022-01-14 | 吕梁学院 | Synthetic method of bindarit |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL28032A (en) * | 1966-08-29 | 1971-08-25 | Acraf | Indazol-3-yl-oxyalkanoic acids and process for the preparation thereof |
| US3470298A (en) * | 1969-01-29 | 1969-09-30 | Acraf | Topical anti-inflammatory composition containing (indazole-3-yl)-oxyalkanoic acids |
| IT1131779B (en) | 1980-07-29 | 1986-06-25 | Acraf | SALT OF THE ACID (1-BENZYL-1H-INDAZOL-3-IL) -OXIACETIC WITH LYSINE AND PROCEDURE FOR ITS PREPARATION |
| IT1189052B (en) | 1981-11-27 | 1988-01-28 | Acraf | CATARACT TREATMENT |
| IT1194564B (en) | 1983-04-18 | 1988-09-22 | Acraf | USE OF BENDAZAC AND ITS SALTS IN THE TREATMENT OF PIGMENTAL RETINITIS |
| IT1197805B (en) | 1986-08-01 | 1988-12-06 | Acraf | METHOD FOR THE TREATMENT OF CONTACT LENSES |
-
1989
- 1989-02-07 IT IT8947620A patent/IT1230441B/en active
-
1990
- 1990-01-22 IL IL9313290A patent/IL93132A/en not_active IP Right Cessation
- 1990-01-23 DE DE69021902T patent/DE69021902T2/en not_active Expired - Lifetime
- 1990-01-23 EP EP90200167A patent/EP0382276B1/en not_active Expired - Lifetime
- 1990-01-23 DE DE199090200167T patent/DE382276T1/en active Pending
- 1990-01-23 DK DK90200167.6T patent/DK0382276T3/en active
- 1990-01-23 AT AT90200167T patent/ATE127115T1/en not_active IP Right Cessation
- 1990-01-23 ES ES90200167T patent/ES2020171T3/en not_active Expired - Lifetime
- 1990-01-24 US US07/470,118 patent/US4999367A/en not_active Expired - Lifetime
- 1990-01-26 NZ NZ232258A patent/NZ232258A/en unknown
- 1990-01-29 ZA ZA90644A patent/ZA90644B/en unknown
- 1990-01-30 IN IN81/CAL/90A patent/IN170957B/en unknown
- 1990-01-30 PE PE1990164654A patent/PE25091A1/en unknown
- 1990-02-02 AU AU49066/90A patent/AU624895B2/en not_active Expired
- 1990-02-05 YU YU20690A patent/YU47943B/en unknown
- 1990-02-05 PL PL90283638A patent/PL163720B1/en unknown
- 1990-02-05 RO RO144074A patent/RO106252B1/en unknown
- 1990-02-05 PL PL90285287A patent/PL163730B1/en unknown
- 1990-02-06 UA UA4743128A patent/UA26852C2/en unknown
- 1990-02-06 FI FI900577A patent/FI102678B/en active IP Right Grant
- 1990-02-06 PT PT93067A patent/PT93067B/en active IP Right Grant
- 1990-02-06 BG BG091122A patent/BG50273A3/en unknown
- 1990-02-06 JP JP2027007A patent/JP2870925B2/en not_active Expired - Lifetime
- 1990-02-06 HU HU90689A patent/HU204793B/en unknown
- 1990-02-06 EG EG6290A patent/EG19170A/en active
- 1990-02-06 CZ CS90563A patent/CZ280121B6/en not_active IP Right Cessation
- 1990-02-06 AR AR90316095A patent/AR247386A1/en active
- 1990-02-06 SK SK563-90A patent/SK56390A3/en not_active IP Right Cessation
- 1990-02-06 PH PH40002A patent/PH26552A/en unknown
- 1990-02-06 RU SU904743128A patent/RU2066318C1/en active
- 1990-02-07 DD DD90342349A patent/DD295363A5/en unknown
- 1990-02-07 CA CA002009503A patent/CA2009503C/en not_active Expired - Lifetime
- 1990-02-07 KR KR1019900001453A patent/KR0145525B1/en not_active Expired - Fee Related
- 1990-02-07 CN CN90100599A patent/CN1046505C/en not_active Expired - Fee Related
- 1990-02-07 DD DD90337657A patent/DD291995A5/en unknown
- 1990-12-20 US US07/632,117 patent/US5112986A/en not_active Expired - Lifetime
-
1991
- 1991-06-05 RU SU914895526A patent/RU2055071C1/en active
- 1991-06-05 RU SU914895540A patent/RU2044729C1/en active
- 1991-11-15 GR GR91300073T patent/GR910300073T1/en unknown
-
1993
- 1993-06-22 LV LVP-93-647A patent/LV10612B/en unknown
- 1993-07-26 GE GEAP19931214A patent/GEP19971030B/en unknown
- 1993-08-17 LT LTIP872A patent/LT3604B/en not_active IP Right Cessation
- 1993-09-15 CN CN93117740A patent/CN1034016C/en not_active Expired - Fee Related
-
1995
- 1995-11-22 GR GR950403284T patent/GR3018165T3/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |